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Basics of Organic Chemistry question

2004 · Shift 0 · Q26
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Basics of Organic Chemistry question

2004 · Shift 0 · Q26

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The IUPACIUPACIUPAC name of the compound is AIEEE 2004 Chemistry - Basics of Organic Chemistry Question 235 English
  1. A
    3,33,33,3-dimethyl - 111 - cyclohexanol
  2. B
    1,11,11,1-dimethyl- 333 -hydroxy cyclohexane
  3. C
    3,33,33,3-dimethyl- 111 -hydroxy cyclohexane
  4. D
    1,11,11,1-dimethyl - 333 - cyclohexanol
View written solutionFree

Correct answer: A

  1. Identify the parent ring and principal functional group

    The compound is a cyclohexane ring containing an −OH-OH−OH group and two methyl groups on the same carbon.

    Since alcohol has higher priority, the parent name must be based on cyclohexanol rather than hydroxycyclohexane.

  2. Number the ring

    In cyclic alcohols, the carbon bearing the −OH-OH−OH group gets locant 111 automatically.

    So the parent is: cyclohexan-1-ol\text{cyclohexan-1-ol}cyclohexan-1-ol which is commonly written as: 1-cyclohexanol\text{1-cyclohexanol}1-cyclohexanol

  3. Locate the methyl substituents

    From the structure, the two methyl groups are attached to carbon 333 of the ring.

    Hence the substituent part is: 3,3-dimethyl3,3\text{-dimethyl}3,3-dimethyl

  4. Write the complete name

    Combining substituent and parent name: 3,3-dimethyl-1-cyclohexanol3,3\text{-dimethyl-1-cyclohexanol}3,3-dimethyl-1-cyclohexanol

  5. Check the options

    • A: 3,33,33,3-dimethyl-111-cyclohexanol ✅ Correct
    • B: 1,11,11,1-dimethyl-333-hydroxy cyclohexane ❌ Alcohol should be principal suffix, not hydroxy prefix
    • C: 3,33,33,3-dimethyl-111-hydroxy cyclohexane ❌ Same issue; should use alcohol suffix
    • D: 1,11,11,1-dimethyl-333-cyclohexanol ❌ Wrong numbering
  6. Final answer

    The correct IUPAC name is: 3,3-dimethyl-1-cyclohexanol\boxed{3,3\text{-dimethyl-1-cyclohexanol}}3,3-dimethyl-1-cyclohexanol​

    So, the correct option is A.

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